Photopolymerizable compositions

Abstract

A photopolymerizable composition is described, which comprises a polymerizable compound containing at least one ethylenically unsaturated double bond and a photopolymerization initiator wherein the photopolymerization initiator is a combination of a 3-keto-substituted cumarin compound and an active halogeno compound. This composition can be easily cured by irradiation with radiation and, therefore, is very useful in the preparation of light-sensitive materials.

What is claimed is: 
     
       1. A photopolymerizable composition comprising a polymerizable compound containing at least one ethylenically unsaturated double bond and a photopolymerization initiator wherein the photopolymerization initiator is a combination of a 3-keto-substituted cumarin compound and an active halogeno compound, and wherein the 3-keto-substituted cumarin compound is at least one member selected from the compounds represented by the general formula (I) or (I'): ##STR8## wherein R 1  is (1) an alkyl group containing from 1 to 10 carbon atoms, (2) a substituted or unsubstituted aryl group containing from 6 to 12 carbon atoms, where the substituent for the substituted aryl group R 1  is a dialkylamino group with the alkyl moiety containing from 1 to 4 carbon atoms, a diarylamino group with the aryl moiety containing from 6 to 10 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, or an alkyl group containing from 1 to 4 carbon atoms, or (3) a --CH═CH) n  R 5  group wherein R 5  is (a) a substituted or unsubstituted aryl group containing from 6 to 14 carbon atoms where the substituent for the substituted aryl group R 5  is a dialkylamino group with the alkyl moiety containing from 1 to 4 carbon atoms, a diarylamino group with the aryl moiety containing from 6 to 10 carbon atoms, an alkoxy group containing from 1 to 4 carbon atoms, or an alkyl group containing from 1 to 4 carbon atoms, or (b) a heterocyclic group in which the number of carbon atoms and hetero atoms constituting the ring is from 5 to 15; and n is 1 or 2; and R 2 , R 3 , R 4 , R 2  ', R 3  ', and R 4  ' are each hydrogen, an alkoxy group containing from 1 to 6 carbon atoms, an alkyl group containing from 1 to 4 carbon atoms, a dialkylamino group with the alkyl moiety containing from 1 to 4 carbon atoms, a hydroxy group, a halogen atom, a nitro group, or a 5-membered or 6-membered heterocyclic group, and two or three of R 2 , R 3  and R 4  or R 2  ', R 3  ' and R 4  ' may combine together to form a condensed ring, or a condensed heterocyclic ring in which the number of carbon atoms and hetero atoms constituting the ring is from 5 to 10, and   wherein the active halogeno compound is at least one member selected from the group consisting of aromatic sulfonyl chloride compounds and s-triazine compounds substituted by at least one trihalomethyl group.   
     
     
       2. The photopolymerizable composition as claimed in claim 1, wherein the active halogeno compound is at least one aromatic sulfonylhalide compound selected from the group consisting of 1-naphthalenesulfonyl chloride, 2-naphthalenesulfonyl chloride, 1-anthraquinonesulfonyl chloride, 2-anthraquinonesulfonyl chloride, 1,5-anthraquinonedisulfonyl chloride, and 1,8-anthraquinonedisulfonyl chloride. 
     
     
       3. The photopolymerizable composition as claimed in claim 1, wherein the active halogeno compound is at least one member selected from the compounds represented by the general formula (II): ##STR9## wherein X is a halogen atom; Y is --CX 3 , --NH 2 , --NHR', --NR' 2 , or --OR' (wherein R' is an alkyl group containing from 1 to 4 carbon atoms or an aryl group containing from 6 to 10 carbon atoms); and R is --CX 3 , an alkyl group containing from 1 to 12 carbon atoms, a substituted or unsubstituted aryl group containing from 6 to 12 carbon atoms, an alkenyl group containing from 2 to 12 carbon atoms, or a substituted or unsubstituted aralkenyl group containing from 8 to 20 carbon atoms. 
     
     
       4. The photopolymerizable composition as claimed in claim 1, wherein the weight ratio of the photopolymerization initiator to the polymerizable compound is in the range of from about 1:5 to about 1:1,000. 
     
     
       5. The photopolymerizable composition as claimed in claim 4, wherein the weight ratio of the photopolymerization initiator to the polymerizable compound is in the range of from about 1:10 to about 1:100. 
     
     
       6. The photopolymerizable composition as claimed in claim 1, wherein the weight ratio of the 3-keto-substituted cumarin compound to the active halogeno compound is in the range of from about 30:1 to about 1:30. 
     
     
       7. The photopolymerizable composition as claimed in claim 6, wherein the weight ratio of the 3-keto-substituted cumarin compound to the active halogeno compound is in the range of from about 10:1 to about 1:10.